21–30 of 38 posts
You are much better of then most entrepreneurs: the projects are up and running and are making some money. A lot of people quit their jobs and then get started. And a year of runway is even better!
But I agree to the other comments that you should focus on one of the projects which can really become big.
Re 2: recruit your replacement yourself. Maybe you fins somebody even here in HN?
I would ask to start working part-time and quit if they won't let you.
You'll of course have to be prepared to be fired outright, but odds are if you offer to stay on a while and help them hire and train a replacement, they'll take you up on it and you'll leave with all your social karma intact - which means you may be able to come back later if your startups go belly-up.
Social karma has real value that way, it's worth some effort to maintain.
If your start up is your dream - go for it! You are much better of then most entrepreneurs: the projects are up and running and are making some money. A lot of people quit their jobs and then get started. And a year of runway is even better! But I agree to the other comments that you should focus on one of the projects which can really become big. Re 2: recruit your replacement yourself. Maybe you fins somebody even…
Be honest with the people around you about what you want (part of this means thinking it through yourself...). In a worst case scenario you lose your job. But if you're really ambivalent about leaving, giving notice like this should alleviate any guilt over quitting and being honest should keep you on better terms with people than the alternative. And you never know. Perhaps your boss will give you a raise or otherwise help solve your motivation problems.
In the end, I asked myself "if I could snap my fingers, and tomorrow be out of my day job, without having to go through the social awkwardness of quitting, etc.... Would I do it?" My answer was an instant "yes". That showed me that any threat of the financial instability was not a real concern, but just an excuse for me not wanting to burn bridges.
After that, I was entirely confident in my decision to quit.
#2 suggests you may be underpaid. I'd go to your boss privately and tell him you've thinking about leaving to do a startup because you don't feel challenged at work, and this is hurting your productivity and interest in the job. All of this is true, you're just afraid to say it because of an innate desire for conflict avoidance. Be honest with the people around you about what you want (part of this means thinking it…
Here's my advice regarding sorting out #1 vs #2. The question in my mind is how much each factor is. When I quit my day job, the social pressures/burning bridges aspect of it was a part of my reluctance. But, of course, more financial instability was another. In the end, I asked myself "if I could snap my fingers, and tomorrow be out of my day job, without having to go through the social awkwardness of quitting, etc.…
If you think leaving the job is inevitable, then you should start preparing for that - i.e. work hard, because the last memories in their minds will be the ones that stick the most.
I've been through this, and I have an open invitation to return to an old job because of it. For now I've left it all and I'm building my own company. Just make sure you understand your costs, and make sure you have health insurance. Don't buy into all the crap about - i'm young, i'll just buy the cheapest insurance on the market. The insurance is for the things you don't expect. Not being able to eat or pay rent are small problems, but neither can bankrupt you. Medical costs can. My buddy broke his leg on a mountain; fortunately he has insurance, but if he didn't the costs would have bankrupted him. He's a young and healthy guy otherwise
Also, people start their own companies with far less than 1 year of savings. You'll find, even if you have 5 years of runway, the prospect of jumping the safety of your paycheck is going to be terrifying. Once you do it though, you'll stop thinking about it very quickly. Look at it differently - 1 year of runway may force you to work harder than ever; you know, necessity is the mother of all invention.
Earlier quoted context omitted.
http://www.sproutvideo.com http://www.physicalfix.com
I am really digging the idea of charging $1 for the trial. Care to share how it's effected the quality and quantity of trial users?